The parent family of Obadiah Gildersleeve, Sr. is the Birth Family.
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 | Ens Thomas Gildersleeve, > (1661-1740)
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 | Mary Munn (1663-1722)
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| George Gildersleeve (1687-1739)  |
| Elizabeth Gildersleeve (1701-1705) |
| Elisha Gildersleeve (1697-1774) |
| Dorcas Gildersleeve (1704-1789) |
| Richard Gildersleeve (1695-1738) |
| Moses Gildersleeve (1709- ) |
| Mary Eliza Gildersleeve (1693-1746) |
| Asa Gildersleeve, I (1685-1773) |
| Richard Valentine (1650-1723)
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| Sarah Halstead (1660-1723)
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| Sarah Valentine (1691- ) |
| Thomas Gildersleeve, Jr (1690-1741)
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| Martha Valentine (1690-1725)
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| Philip Gildersleeve, > (1726-1760) |
| Obadiah Gildersleeve, Sr. (1728-1816) |
| Experience Gildersleeve (1730- ) |
| Elizabeth Gildersleeve (1720-1750) |
| Bridget Gildersleeve (1719-1772) |
| Henry Gildersleeve (1724-1790) |
| Thomas Gildersleeve, lll (1716- ) |
| Benjamin Gildersleeve (1718-1771) |
| Mary Gildersleeve (1720- ) |
